Dave Chappelle made a surprise appearance during Maxwell’s set at the Roots Picnic.
The comedian spoke to the crowd during the R&B icon’s headlining set on Saturday (May 31) and praised The Roots for organizing the event and congratulated Maxwell on his career journey.
“This is outstanding. Make some noise Philadelphia, the city of Brotherly Love,” said Chappelle, as seen in a video making the rounds online. “From the front to the back, all I see is beautiful black people. I don’t see no violence, I don’t see no hatred. I just see love and community. I flew all the way from Ohio to fuck with that.”
“When I met Maxwell, I was on a date with the woman that’s now my wife. He was a bartender at a restaurant in Union Square, you remember?” Chappelle recalled, referencing his now-wife Elaine Chappelle whom he married in 2001. “If I said this to this n***a, ‘orange juice and cranberry,’ he’ll choke me to death,” he joked, as the crowd laughed.
After the comedian exited, Maxwell stepped back in front of the mic and offered his own recollection of their early days.
“I don’t think Dave remembers but when I saw him, I walked up to him and I said, ‘You know, you’re really funny, bro. You should really keep doing this.’ And this is really true,” Maxwell said. “I walked up to him and told him that I was a waiter. God is good is all I’m trying to tell y’all.”
Maxwell was a late addition to the 2025 Roots Picnic lineup after D’Angelo dropped out due to an extended recovery from surgery.
The annual festival, founded by The Roots, continues today (June 1) at Philadelphia’s Mann Center for the Performing Arts and features artists including Lenny Kravitz, Meek Mill, GloRilla, Miguel, Tems, Latto, Pusha T, 2 Chainz, Jeezy, Jagged Edge, and more.
